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Synthesis and thermal stability of secondary sugar allyltin derivatives

✍ Scribed by Sławomir Jarosz; Katarzyna Szewczyk; Anna Zawisza

Book ID
104359853
Publisher
Elsevier Science
Year
2003
Tongue
English
Weight
666 KB
Volume
14
Category
Article
ISSN
0957-4166

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✦ Synopsis

Reaction of sugar allylic mesylates with tri-n-butyltin cuprate affords the primary and secondary allyltin derivatives: Sug-CH CH-CH 2 SnBu 3 and Sug-CH(SnBu 3 )-CH CH 2 with the latter predominating. The S N 2% addition led almost exclusively to one isomer with the S configuration at the newly created stereogenic center. Only traces of the opposite R isomer were formed. Both stereoisomers of secondary allyltins decompose at high temperature (140°C) with elimination of the tin moiety and opening of the sugar ring. The main S isomer gives the dienoaldehyde CH 2 CH-CH CH-[(CHOR) 3 ]-CHO with the cis geometry across the internal double bond. The minor R isomer provides the trans dienoaldehyde under the same conditions. These results strongly suggest the concerted (E2) mechanism of thermal decomposition of secondary sugar allyltin derivatives.

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